TWI572594B - 卡巴利他索（ｃａｂａｚｉｔａｘｅｌ）之結晶型及其製備方法 - Google Patents
卡巴利他索（ｃａｂａｚｉｔａｘｅｌ）之結晶型及其製備方法 Download PDFInfo
- Publication number
- TWI572594B TWI572594B TW101147230A TW101147230A TWI572594B TW I572594 B TWI572594 B TW I572594B TW 101147230 A TW101147230 A TW 101147230A TW 101147230 A TW101147230 A TW 101147230A TW I572594 B TWI572594 B TW I572594B
- Authority
- TW
- Taiwan
- Prior art keywords
- hydroxy
- ethyl acetate
- epoxy
- dimethoxy
- taxane
- Prior art date
Links
- BMQGVNUXMIRLCK-OAGWZNDDSA-N cabazitaxel Chemical compound O([C@H]1[C@@H]2[C@]3(OC(C)=O)CO[C@@H]3C[C@@H]([C@]2(C(=O)[C@H](OC)C2=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=3C=CC=CC=3)C[C@]1(O)C2(C)C)C)OC)C(=O)C1=CC=CC=C1 BMQGVNUXMIRLCK-OAGWZNDDSA-N 0.000 title description 6
- 229960001573 cabazitaxel Drugs 0.000 title description 6
- 238000004519 manufacturing process Methods 0.000 title description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 161
- 239000012453 solvate Substances 0.000 claims description 45
- ZVAFCKLQJCZGAP-WDEREUQCSA-N (2r,3s)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoic acid Chemical compound CC(C)(C)OC(=O)N[C@H]([C@@H](O)C(O)=O)C1=CC=CC=C1 ZVAFCKLQJCZGAP-WDEREUQCSA-N 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 4
- 239000004593 Epoxy Substances 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 230000008859 change Effects 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 22
- 239000013078 crystal Substances 0.000 description 20
- 238000000634 powder X-ray diffraction Methods 0.000 description 14
- 238000004817 gas chromatography Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 206010028980 Neoplasm Diseases 0.000 description 6
- 201000011510 cancer Diseases 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- 206010060862 Prostate cancer Diseases 0.000 description 5
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- 239000010949 copper Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- -1 therapeutic activity Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004807 desolvation Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- 230000008863 intramolecular interaction Effects 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 102000054765 polymorphisms of proteins Human genes 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/14—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Urology & Nephrology (AREA)
- Epoxy Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11306644 | 2011-12-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201329056A TW201329056A (zh) | 2013-07-16 |
| TWI572594B true TWI572594B (zh) | 2017-03-01 |
Family
ID=47559607
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW101147230A TWI572594B (zh) | 2011-12-13 | 2012-12-13 | 卡巴利他索（ｃａｂａｚｉｔａｘｅｌ）之結晶型及其製備方法 |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US9309210B2 (enExample) |
| EP (1) | EP2791122B1 (enExample) |
| JP (1) | JP6025861B2 (enExample) |
| TW (1) | TWI572594B (enExample) |
| WO (1) | WO2013088335A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2926551A1 (fr) | 2008-01-17 | 2009-07-24 | Aventis Pharma Sa | Formes cristallines du dimethoxy docetaxel et leurs procedes de preparation |
| TWI526437B (zh) * | 2011-09-09 | 2016-03-21 | 台灣神隆股份有限公司 | 卡巴他賽之結晶型 |
| WO2013088335A1 (en) * | 2011-12-13 | 2013-06-20 | Aventis Pharma S.A. | Crystalline form of cabazitaxel and process for preparing the same |
| WO2013134534A2 (en) * | 2012-03-08 | 2013-09-12 | Plus Chemicals S.A. | Solid state forms of cabazitaxel and processes for preparation thereof |
| CN102746258B (zh) * | 2012-07-25 | 2015-02-04 | 重庆泰濠制药有限公司 | 卡巴他赛的结晶形式及其制备方法 |
| US20150315164A1 (en) * | 2012-12-31 | 2015-11-05 | Shilpa Medicare Limited | Process for preparing amorphous cabazitaxel |
| EP2815749A1 (en) | 2013-06-20 | 2014-12-24 | IP Gesellschaft für Management mbH | Solid form of 4-amino-2-(2,6-dioxopiperidine-3-yl)isoindoline-1,3-dione having specified X-ray diffraction pattern |
| WO2015000165A1 (zh) * | 2013-07-04 | 2015-01-08 | 北京新天宇科技开发有限公司 | 二甲氧基多西紫杉醇一丙酮化物的稳定转化物及其结晶形式、以及它们的制备方法 |
| EP2865674A1 (en) | 2013-10-23 | 2015-04-29 | INDENA S.p.A. | Crystalline solvate forms of Cabazitaxel |
| EP2865675A1 (en) | 2013-10-23 | 2015-04-29 | INDENA S.p.A. | A crystalline anhydrous form of Cabazitaxel, process for the preparation and pharmaceutical compositions thereof |
| WO2015087228A1 (en) * | 2013-12-10 | 2015-06-18 | Mylan Laboratories Ltd. | Process for the preparation of cabazitaxel and its solvates |
| JP2019501953A (ja) | 2016-01-15 | 2019-01-24 | 珠海貝海生物技術有限公司Ｚｈｕｈａｉ Ｂｅｉｈａｉ Ｂｉｏｔｅｃｈ Ｃｏ．，Ｌｔｄ． | カバジタキセル及びヒト血清アルブミンを含む組成物及び製剤 |
| CN112055588B (zh) | 2018-04-20 | 2023-09-08 | 珠海贝海生物技术有限公司 | 卡巴他赛的制剂和组合物 |
| CN113429369B (zh) * | 2021-07-23 | 2022-12-02 | 无锡紫杉药业有限公司 | 一种高效的卡巴他赛纯化方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200944510A (en) * | 2008-01-17 | 2009-11-01 | Aventis Pharma Sa | Crystalline forms of dimethoxy docetaxel and methods for the preparation thereof |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5847170A (en) | 1995-03-27 | 1998-12-08 | Rhone-Poulenc Rorer, S.A. | Taxoids, their preparation and pharmaceutical compositions containing them |
| MA23823A1 (fr) | 1995-03-27 | 1996-10-01 | Aventis Pharma Sa | Nouveaux taxoides, leur preparation et les compositions qui les contiennent |
| US6346543B1 (en) | 1998-08-17 | 2002-02-12 | Aventis Pharma S.A. | Use of a taxoid to treat abnormal cell proliferation in the brain |
| FR2859996B1 (fr) | 2003-09-19 | 2006-02-03 | Aventis Pharma Sa | Solvat acetonique du dimethoxy docetaxel et son procede de preparation |
| JP5566466B2 (ja) * | 2009-10-29 | 2014-08-06 | アバンテイス・フアルマ・エス・アー | カバジタキセルの新規の抗腫瘍的使用 |
| TWI526437B (zh) | 2011-09-09 | 2016-03-21 | 台灣神隆股份有限公司 | 卡巴他賽之結晶型 |
| PL2785701T3 (pl) * | 2011-11-28 | 2019-08-30 | Fresenius Kabi Oncology Limited | Krystaliczna postać kabazytakselu i sposób jej otrzymywania |
| WO2013088335A1 (en) * | 2011-12-13 | 2013-06-20 | Aventis Pharma S.A. | Crystalline form of cabazitaxel and process for preparing the same |
-
2012
- 2012-12-11 WO PCT/IB2012/057170 patent/WO2013088335A1/en not_active Ceased
- 2012-12-11 EP EP12815825.0A patent/EP2791122B1/en active Active
- 2012-12-11 JP JP2014546702A patent/JP6025861B2/ja active Active
- 2012-12-13 TW TW101147230A patent/TWI572594B/zh not_active IP Right Cessation
-
2014
- 2014-06-11 US US14/301,740 patent/US9309210B2/en active Active
-
2016
- 2016-04-07 US US15/092,919 patent/US20160318888A1/en not_active Abandoned
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200944510A (en) * | 2008-01-17 | 2009-11-01 | Aventis Pharma Sa | Crystalline forms of dimethoxy docetaxel and methods for the preparation thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2015500331A (ja) | 2015-01-05 |
| JP6025861B2 (ja) | 2016-11-16 |
| US9309210B2 (en) | 2016-04-12 |
| US20160318888A1 (en) | 2016-11-03 |
| US20140343133A1 (en) | 2014-11-20 |
| WO2013088335A1 (en) | 2013-06-20 |
| EP2791122B1 (en) | 2019-01-23 |
| EP2791122A1 (en) | 2014-10-22 |
| TW201329056A (zh) | 2013-07-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |